Back to EveryPatent.com
United States Patent | 5,552,091 |
Kumar | September 3, 1996 |
Described are novel reversible photochromic benzopyran compounds, examples of which are compounds substituted at the 2-position of the pyran ring with a dibenzo-fused 5 member heterocyclic compound; other enumerated substituents at the other 2-position of the pyran ring; and a substituted or unsubstituted benzo, benzothieno or benzofurano group fused to the benzo portion of the benzopyran. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel benzopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
Inventors: | Kumar; Anil (Pittsburgh, PA) |
Assignee: | PPG Industries, Inc. (Pittsburgh, PA) |
Appl. No.: | 497516 |
Filed: | June 30, 1995 |
Current U.S. Class: | 252/586; 548/440; 549/42; 549/383; 549/389; 549/457 |
Intern'l Class: | G02B 005/23; C07D 209/82; C07D 333/50; C07D 311/78 |
Field of Search: | 252/586 549/42,383,389,457 548/440 |
3562172 | Feb., 1971 | Ono et al. | 252/300. |
3567605 | Mar., 1971 | Becker | 204/158. |
3578602 | May., 1971 | Ono et al. | 252/300. |
4215010 | Jul., 1980 | Hovey et al. | 252/300. |
4342668 | Aug., 1982 | Hovey et al. | 252/586. |
4637698 | Jan., 1987 | Kwak et al. | 351/163. |
4816584 | Mar., 1989 | Kwak et al. | 544/71. |
4818096 | Apr., 1989 | Heller et al. | 351/163. |
4826977 | May., 1989 | Heller et al. | 544/70. |
4880667 | Nov., 1989 | Welch | 427/160. |
4931219 | Jun., 1990 | Kwiatkowski et al. | 252/160. |
4990287 | Feb., 1991 | Bennion et al. | 252/586. |
5066818 | Nov., 1991 | Gemert et al. | 549/389. |
5200116 | Apr., 1993 | Heller | 252/586. |
5238981 | Aug., 1993 | Knowles | 549/389. |
5244602 | Sep., 1993 | VanGemert | 252/586. |
5274132 | Dec., 1993 | VanGemert | 549/389. |
5384077 | Jan., 1995 | Knowles | 252/586. |
5405958 | Apr., 1985 | VanGemert | 544/71. |
5411679 | May., 1995 | Kumar | 252/586. |
5429774 | Jul., 1995 | Kumar | 252/586. |
Foreign Patent Documents | |||
62-195383 | Aug., 1987 | JP. | |
7-41758 | Feb., 1995 | JP. | |
7-48363 | Feb., 1995 | JP. | |
7-48566 | Feb., 1995 | JP. | |
7-48567 | Feb., 1995 | JP. |
Friedel-Crafts and Related Reactions, George A. Olah, Interscience Publishers, vol. 3 Chapter XXXI, pp. 1-8, 1964. "Regioselective Friedel Crafts Acylation of 1,2,3,4-Tetrahydroquinoline and Related Nitrogen Heterocycles: Effects of NH Protective Groups and Ring Size", Ishihara, Y., et al., J. Chem. Soc., Perkin Trans. 1, pp. 3401-3406, 1992. Heterocyclic Compounds, R. C. Elderfield, 1951, vol. 2, Chapters 3 and 5, pp. 123-144, pp. 164-174. The Chemistry of Heterocyclic Compounds, H. D. Hartough et al., 1954, vol. 7, Chapter IV, pp. 225-282. Advances in Heterocyclic Chemistry, A. R. Katritzky et al., 1974, vol. 16, Chapter V. Akermark et al., Acta Chemica Scandinavica, vol. 13, 1959, pp. 1855-1862. S. Granowitz et al., Acta Pharm. Suec., vol. 15, 1978, pp. 337-360. J.A.C.S. vol. 61, Apr. 1939, pp. 951-956; Dibenzofuran. IX Metalation of Some Derivatives. J.A.C.S. vol. 87 (2), 1965, pp. 213-217; The Electron Spin Resonance Spectra of the Dibenzothiophene Radical Anion and Its Isologs and the Electronic Structure of Conjugated Sulfur-Containing Heterocycles. J.A.C.S. vol. 62, Mar. 1940, pp. 667-669. Dibenzofuran. XVIII. Isomeric Metalation Products of Some Phenols and Their Methyl Ethers. |
TABLE 1 __________________________________________________________________________ COMPOUND LAMBDA MAX SENSITIVITY OD BLEACH RATE EXAMPLE BAND A BAND B .DELTA.OD/MIN @ SAT T 1/2(SEC.) __________________________________________________________________________ 1 439 -- 0.69 0.32 61 2 444 524 0.27 0.20 245 3 448 510 0.47 0.97 800 4 452 502 0.46 0.54 451 5 446 528 0.31 0.41 508 6 416 442 0.20 0.25 406 __________________________________________________________________________